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Condensation fluorous-tagged

For this purpose, perfluorooctanesulfonyl-tagged benzaldehydes were reacted with 1.1 equivalents of a 2-aminopyridine (or 2-aminopyrazine), 1.2 equivalents of an isonitrile, and a catalytic amount of scandium(III) triflate [Sc(OTf)3] under micro-wave irradiation in a mixture of dichloromethane and methanol (Scheme 7.85). A ramp time of 2 min was employed to achieve the pre-set temperature, and then the reaction mixture was maintained at the final temperature for a further 10 min. The fluorous tag constitutes a multifunctional tool in this reaction, protecting the phenol in the condensation step, being the phase tag for purification, and serving as an acti-... [Pg.353]

The time consuming chromatographical purification of heterocycles 28 and 29 slowed down the rate of library production. A phase separation using fluorous chemistry was employed by Zhang and Lu to address the workup and purification of fused 3-aminoimidazo[ l,2-a]pyridines (such as 30) [54]. Thus, attachment of a perfluorooctanesulfonyl tag to aldehydes and subsequent Ugi three-component microwave-assisted condensations with 2-aminopyridines and isocyanides furnished the desired heterocycles 30, which were conveniently isolated by fluorous solid-phase extraction. The fluorous tag could be subsequently used as an activating group in the post-condensation modifications, such as Suzuki-Miyaura cross-coupling reactions. [Pg.66]

The synthesis of small arrays of organic compounds derived from multicomponent condensations was recently reported by Studer et al. (119). A 10-member amino acid amide library L7 (Fig. 8.21) was prepared using the fluorous Ugi ( Flugi ) condensation, and another 10-member dihydropyrimidine library L8 (Fig. 8.21) was prepared using the Biginelli ( Fluginelli ) condensation adapted to the fluorous phase. The key intermediates for library preparation were the silyl bromide 8.36, prepared from a fluorous iodide (120), and the acyl bromide 8.37 and the acid 8.38, prepared from an orthothiobenzoate (121), as shown in Fig 8.21. The structure of the fluorous tag was... [Pg.365]

A fluorous tagged version of 1 has also been prepared and used as a separation friendly Mukaiyama condensation reagent (19) for amide formation.9... [Pg.465]

Scheme 17 illustrates another fluorous sulfonate-based synthesis of library scaffolds. The tagged substrates were taken through aldol condensation and cycloaddition reactions to form the pyrimidine ring 18. The intermediates were then reacted with boronic acids for Suzuki reactions to form biaryl compounds 19 [31], reacted with HCO2H to give traceless detagged products 20 [34], or reacted with amine to form products 21 [33]. [Pg.159]

Both Siegel et al. (122) and Lawrence et al. (123) have described automated systems for the purification of small arrays of amines and amides. A 48-member array of P-amino alcohols prepared from epoxides and amines was purified using SPE by Shuker et al. (124). Blackburn et al. (125) have described the purification of a 60-member 3-aminoimidazo[l,2-fl]pyridine array obtained from a multiple-component condensation, and Bussolari et al. (126) purified a small array of phenylpropyl amines obtained from dihydrocoumarins and amines. A few applications where ion-exchange resins have been substituted with other solid phases have also recently appeared. For example, the purification of several carbohydrate arrays tagged as hydrophobic O-laurates using Ci8 silica producing up to 10-30 mg of >90% pure individuals was described by Nilsson et al. (127), and Curran et al. purified fluorous-... [Pg.369]

Scheme 3.17 Fiuorous variants of the Ugi (above) and Bigineiii muiti-component reactions (beloiv) enabie the purification of the primary fluorous condensation products (not shown in this scheme) by simple two- or three-phase extraction, followed by "traceless" cleavage of the fluorous silyl tag with TBAF [5]. Scheme 3.17 Fiuorous variants of the Ugi (above) and Bigineiii muiti-component reactions (beloiv) enabie the purification of the primary fluorous condensation products (not shown in this scheme) by simple two- or three-phase extraction, followed by "traceless" cleavage of the fluorous silyl tag with TBAF [5].
The introduction of additional substituent groups in combination with the discriminating perfluoroalkyl labels during the synthetic sequence enables convenient preparation and subsequent separation of relatively large libraries. For the library of 100 mappicine derivatives outlined in Scheme 3.20, 300 reactions would be required for the conventional, sequential approach. By application of fluorous mixture synthesis this was condensed into 26 steps. In addition, four tagging and 100 detagging operations are required to obtain the full, unprotected 100-member library from unprotected starting materials. [Pg.195]


See other pages where Condensation fluorous-tagged is mentioned: [Pg.181]    [Pg.354]    [Pg.14]    [Pg.201]    [Pg.102]    [Pg.93]    [Pg.42]    [Pg.188]    [Pg.181]    [Pg.766]    [Pg.181]    [Pg.309]    [Pg.98]    [Pg.207]   
See also in sourсe #XX -- [ Pg.354 ]




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